


He Wears Short Skirts

by TheIttyBitty



Category: Supernatural
Genre: Cas is a cutie, Crossdressing, Friends to Lovers, Halloween, M/M, mentions of abuse
Language: English
Status: Completed
Published: 2015-10-09
Updated: 2015-10-09
Packaged: 2018-04-25 13:20:27
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,418
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4962109
Author URL: https://archiveofourown.org/users/TheIttyBitty/pseuds/TheIttyBitty
Summary: <blockquote class="userstuff">
              <p>In which Dean thinks it would be funny to see Cas in drag, but it's really not funny at all.</p>
            </blockquote>





	He Wears Short Skirts

**Author's Note:**

> I'm putting Cas and Dean around 18-19 years old. 
> 
> I meant this fic to be much more Halloween-ish than it turned out. So i'm sorry about that.

It’s Dean’s own fault, this situation. He’s the one that proposed the bet. A stupid bet, to see who could land more balls of paper in a trashcan. Stupid. But he gets bored, alright?

Cas had agreed, unaware that Dean is _boss_ at throwing shit at other shit, and lost miserably. But Cas’ terrible terrible aim is not the problem.

No, the problem is the stakes. At the time, Dean had thought it would be just _hilarious_ to see Cas in drag. So, he had bet that the loser wear Jo’s clothes for Halloween. The three of them were going to be at the Winchester house on Halloween anyway, passing out candy and watching scary movies. 

Their days of trick-or-treating are apparently over, now that John and Mary have decided that _they_ want to go out for Halloween and passed the candy responsibilities to their oldest son and his friends.

So, _the problem_ is Cas. Jo showed up a couple hours ago right after Cas and dragged the boy upstairs to the bathroom where she not only squeezed him into her clothes, but put some makeup on him as well.

And now they’ve come back down the stairs and _here is the problem_ : Cas does not look silly. He does not look funny. He looks fucking hot.

Dean almost spits his coke all over the coffee table whenever Cas walks into the living room and takes his seat next to Dean on the couch. He opens his arms.

“Happy?” He asks.

Dean nods tightly. “Mmhhm.” He says, because he doesn’t actually trust himself to speak.

Jo comes in a second later, looking knowing and smug.

Cas has on a miniskirt. A tight (so, so tight), short, black one that only comes to about mid-thigh. He’s also got on black tights, a thin blue v-neck, and a pair of his own faded black boots because none of Jo’s shoes fit him. Eyeliner is thick around his eyes, smoky and dark, and mascara elongates his eyelashes. His lips shimmer pinkly with lipgloss and Dean has the sudden urge to taste it.

Dean turns back to the television, absolutely not looking at Cas’ legs ensconced in those tights. 

“What are we watching?” Cas wonders.

Dean clears his throat. “Ah, Buffy was on.”

“Oh, good!” Cas says, propping his huge booted feet up on the coffee table and leaning back into the couch. “I love this one! Alyson Hannigan is a gem.”

Dean should tell Cas to get his feet off of the coffee table, like he normally does when his friend _never fails_ to do it even though he knows he shouldn’t, but every time he goes to do it it’s like Dean’s voice dries up. He sees Cas’ legs in those goddamn tights and he forgets everything he means to say. So he stays quiet, leaning away from Cas in a way that he hopes in inconspicuous, gripping his coke like it’s a life preserver. But of course Cas, being Cas, slowly leans more and more toward Dean throughout the show, until his head is resting on Dean’s shoulder.

Dean coughs, shifting uncomfortably. He sort of wants to tell Cas to get off him, but he also sort of wants to tell Cas to get under him, so there’s that. 

Of course, he generally doesn’t have any problem with Cas leaning on him, so if he says anything now it’ll probably be weird. Fuck, he’s overthinking this. He knows he’s overthinking this. It shouldn’t be a big deal. But his heart’s going a mile a damn minute, his stomach is churning in a way that’s uncomfortable, but not sickly, and he feels like he’s breathing too loudly. Is he breathing too loudly?

“You okay?” Comes Cas’ voice, lazy and unbothered by the type of thoughts that plague Dean.

“Yep.” Dean says shortly. 

Cas sits up a little, reaches up to rub Dean’s shoulder. “You seem tense.”

“Uh,” Dean says, tensing even more at the touch of Cas’ fingers. “This, uh, this episode weirds me out.”

Jo snickers from her place in John’s EZ chair, and Dean glares at her. She knows exactly what she did, that fuckin’ asshole. Cas looks, confused, from Dean to the tv, back to Dean, to Jo. Because this is a fucking vanilla season 1 episode and there’s no reason for it to bother Dean and they all know it.

“Oh…. kay.” Cas says slowly. He seems to realize that he’s missing something, but can’t quite figure out what. He sits back, frowning. He’s not leaning on Dean anymore, which is somehow both frustrating, and a relief.

The rest of the night goes… oddly. They watch TV and Dean is awkward. They give candy to trick-or-treaters dressed as little dragons and witches and ninjas and Dean is awkward. He fumbles over his words and he’s stiff and just generally weird. Cas notices. He asks Dean if somethings wrong so many times that Dean has run out of excuses. 

After a while Jo goes home and it’s just Dean and Cas, alone. 

“You know you can, uh, change back into your clothes, right? I mean, that bet didn’t say you had to _stay_ in them.”

Beside him, Cas shrugs. He plucks at the thin material of his shirt. “I kinda like it.” He says, grinning. “Makes me feel pretty.” He stretches and crosses his arms behind his head. 

Dean snorts. “You’re a very pretty girl, Cas.”

“I’m a boy, Dean. A very pretty _boy_.”

Dean laughs, and everything feel normal for a second before he reaches over and claps a hand on Cas’ knee, which is normally something he wouldn’t think twice about, but this time there’s no thick denim in between his hand and Cas’ leg. This time there’s just that thin, legging materiel, all soft and sort of stretchy, and it just makes Dean feel strange. He jerks his hand back, quickly, and Cas gives him a weird look, but he doesn’t comment. They’re quiet for a while, more so than usual. About the time they run out of candy, the time Cas usually heads home, he starts getting fidgety. 

“Hey, uh,” He says, frowning. “So, Micheal’s home from school for a few days and-”

“Yeah, man.” Dean interrupts, aware of the question Cas is going to ask before he even poses it. “You can stay here.”

Things might be a little weird right now, but he’s not going to turn Cas away because of this. Cas always stays over when Micheal comes around, ‘cause he’s an asshole of a step-brother and he likes to knock Cas around, and that’s not cool, okay? Honestly, Dean doesn’t know why Cas even feels the need to ask anymore. He should know by now that he can always stay. 

“C'mon man, I’m beat.” He says. He flips off the television and heads up the stairs, not even checking behind himself to see if Cas is following, because he knows that he is. He gets an old t-shirt and a pair of pajama pants from his dresser and tosses them to Cas, where he stands by the door. 

Cas smiles at him, soft. “Thanks.” He says, and he’s just Cas. Yeah, he’s hot as hell, but he’s Dean’s friend first, and Dean cares about him. Honestly, truly. 

“No problem.” He says. 

Cas plods off to the bathroom to change, leaving Dean to do the same, and when he gets back he tosses Jo’s clothes onto the floor and slips into the unoccupied side of Dean’s bed. It’s not huge, but it’s big enough, and they’ve been sharing beds for years, so it’s not a big deal. 

Cas looks different now, normal, in soft pajamas, face divested of makeup. He’s no less beautiful, if Dean is being completely honest, but it’s in a way he can deal with. 

Cas turns onto his side to face Dean, features soft and familiar. Dean turns on his side too.

“How long has Micheal been back?” He asks. 

Cas’ eyes shift away. “Couple days.” 

“Dude!” Dean exclaims. “Why didn’t you tell me?”

Cas shrugs one shoulder. “Didn’t wanna be a bother.”

“I can’t believe you still think you’re a bother. Honestly, man, that’s kind of insulting.”

“Sorry.” Cas sighs.

Dean shakes his head. “I’m messin’ with you, man. But really, you know can stay anytime.”

“I know. But I always feel like I’m-”

“You’re not intruding. And you’re not a burden.” Dean interrupts. Because for some damn reason Cas still thinks shit like that. 

“Okay.” He whispers. 

“He hurt you?”

“Only a little.” 

Dean clenches his fist in the blanket, anger boils in his stomach. One day. One day he’s gonna kick Micheal’s ass.

“Where at?”

Cas pushes the blanket down and pulls his shirt up to show Dean a big purpling bruise over one of his ribs.

  
“Cas…” Dean breathes. Before he thinks about it he reaches out and touches the tips of his fingers to the skin just below the bruise. “What did he do?”

Cas pulls his shirt back down, not meeting Dean’s eyes. “Pushed me into a table.”

“That fucking dick!” Dean spits. 

“It’s not a big deal.” Cas says.

“Like hell it’s not! That’s not okay, Cas! How can you think it’s not a big deal.”

“Because I’m here now.” Cas says. “I’m safe with you.”

Dean goes quiet. He’s never exactly sure what to do when they talk about Micheal, because Cas always insists that it isn’t a big deal, but it feels like a freaking huge deal. And Cas always stays with Dean when Micheal comes over, and that has to mean something, right? Cas is afraid of Micheal, of what Micheal might do, and that’s a big deal. And then sometimes Cas says shit like he’s safe with Dean, and that’s a big deal too. 

“I won’t let anything happen to you.” Dean tells him. “I promise.”

Cas smiles, Dean can see his eyes crinkle in the dark. “I know. I know, Dean.”

 

After a while they hear Mary and John get home, and Sam is staying the night with friends, so he won’t be back until tomorrow. Dean closes his eyes and tries to sleep, but he can’t. He thinks, he just thinks. Does it too much, Mom says. Thinks until he’s all worked up. She’s right, and soon he’s thought himself into a mood. 

“Cas,” He whispers. “You awake?”

“Hmm?” Says Cas. “’m awake.”

“You wanna egg Micheal’s car?” 

Cas raises his head a little, just enough to glare at the clock on Dean’s bed table. “It’s two-thirty in the morning, Dean.” He grunts.

“Yeah, we’re not gonna egg somebody’s car in the daytime, come on. We can go to Denny’s after, get somethin’ to eat? Pancakes, yeah?”

Cas looks at him for a few moments, purses his lips. “What about waffles?” 

“We can get waffles.”

“Okay, fine.”

Dean grins. “Awesome.”

 

They get up quietly, Dean flicks on the light and they get dressed turned away from each other. When Dean turns back, he stops short. 

“Uh, Cas…”

Cas looks up expectantly. “Yeah?”

Dean raises his eyebrows. 

Cas smiles a little, picking at his nails nervously. He obviously knows what Dean’s talking about.

“I like them.” He says quietly. 

The tights. He’s wearing the tights, and the skirt. He has on his big boots, but instead of the v-neck, he’s wearing a big gray sweater. His hair is rumpled, his mouth and eyes are soft from sleep. He’s… fucking cute. Really damn cute.  
Cas goes over to Dean’s dresser, where Jo apparently left some of her makeup, and picks up an eyeliner pencil.

“Help me put this on?” Cas asks, holding the pencil out to Dean.

“I- I don’t know how to do that, dude.”

“It just goes on the edges of my eyelids. It’s easy.” He presses the pencil into Dean’s hand and sits back on the bed. He tilts his head back and closes his eyes. 

“I’m gonna fuck it up.” Dean argues.

“I believe in you.”

Dean huffs, but he steps up to Cas, in between his knees. He puts a hand on the side of Cas’ face to hold him still, and presses the pencil to the line of Cas’ eyelid. 

“Not too hard.” Cas says softly.

Dean is fighting to keep his breathing steady, but he’s so close to Cas, close to his soft lips and his tanned skin. His hand shakes a little. 

“Fuck.”

“It’s fine.” Cas says. “I’ll smooth it out after.”

Dean grumbles, but he finishes both eyes, and he thinks maybe he didn’t do too badly. 

“There ya go.” He says. 

Cas finally opens his eyes, and yeah, he did alright. The liner makes Cas’ eyes pop, just like earlier. He smiles up at Dean, whos hand is still on his face, and Dean sort of thinks he might be having a heart attack for a second, as fast as it’s racing. 

He steps back, clearing his throat, rubbing his hands on the sides of his jeans. “You good?”

Cas nods. “Lets go.”

They sneak out of the house, drive Cas’ little Tracker to the nearest grocery store, and and buy about five dozen eggs, people look at Cas funny, but he doesn’t seem to notice. They park about a block away from Cas’ house and sneak up to it in the dark. They’re not as quiet as they probably should be, but they’re carrying a ton of eggs, and also Cas keeps laughing. 

“Shh,” Says Dean, but he’s caught the excitement too, and everything seems funny. He laughs too, stifling the noise in his elbow when he can. They smash all of the eggs on Micheal’s car, and it feels awesome. 

They run back to Cas’ car, and they let themselves laugh loudly. They drive to the nearest Denny’s and get themselves a booth and several piles of waffles, which they consume with fervor. Their waitress keeps giving them funny little smiles that Dean doesn’t understand until she brings Cas a refill on his tea, looks at Cas, then Dean, and says, “You guys are so cute, seriously. How long have you been together?”

They both freeze. Dean’s eyes dart to Cas, and Cas looks at Dean. 

“Oh, no-” Says Dean.

“That’s not-” Cas says at the same time.

“We’re-”

“I mean-”

“Well-”

They both fall silent. Dean clears his throat. “We’re not, uh… dating.” He says.  
“Oh!” Says the waitress. “Oh, i’m so sorry! I- I just assumed-” Her cheeks are steadily turning a bright red, and Dean feels sorry for her. It’s not like he can blame her for thinking it, his feelings for Cas aren’t exactly platonic, he’s just not used to people picking up on it. 

He waves her apologies aside. “It’s fine.” He tells her. 

“Alright. Um. I’ll just… get you a refill.” She says, turning and walking quickly away, apparently forgetting that she only just finished refilling both of their drinks. 

Dean and Cas sit in silence for a few minutes, it’s not exactly awkward. But there’s… something else. Every time Dean looks up he finds Cas looking at him, this strange expression on his face. He looks a little confused, a little curious, and sort of like he’s concentrating on something too. 

“You okay, man?” Dean asks him after the fifth time he finds Cas looking at him like that.

Cas’ eyes dart away. “Hmm? Oh, yes. I was, um…” Abruptly he picks his fork back up. “These are very good waffles.” He says, and proceeds to stuff his face. 

Dean shrugs, and goes back to eating his own waffles. 

The waitress doesn’t come back right away, presumably because she realized she’d just given them refills. She does come back a little later though, and Dean asks for the check. 

“Separate?” The waitress asks.

“Yes.” Says Cas.

“Nah, man, I got it.” Dean waves him off.

“You don’t have to, Dean.”

Dean gives him a “don’t be an idiot” look, Cas raises an eyebrow. 

Dean turns to the waitress. “I got it.” He tells her. 

She squints at him, as if trying to figure something out, but she doesn’t say anything. When she brings the check back, she hands it to him, smiling kindly. 

It’s chilly when they leave, really chilly, and Cas has his arms wrapped around his torso, shivering despite his sweater. Dean shrugs off his jacket and puts it over Cas’ shoulders.

Cas looks up, startled, at the weight of the fabric, but when he realizes what Dean has done  his eyes light up, he smiles big. Dean’s stomach flip-flops wildly, he smiles back. When they get back to Cas’ car, Dean leans on the side of it instead of getting in. Cas stands next to the driver’s side door.

“I don’t really feel like going home. Can we stay out?”

Cas shrugs. “Tomorrow _is_ Sunday. What do you want to do?”

“Let’s drive to the river. We can take a walk.”

“Take a walk?”

“Yeah. You like walks.”

“Well, yeah. I didn’t think you did, though.”

Dean shrugs. “I like walks with you.”

Cas’ mouth falls open. He makes a small squeaking sound before quickly shutting his mouth, opening the car door, and getting inside. Dean follows. Cas doesn’t say anything more though, he just starts up the car and drives them toward the river. It’s a short drive, and they park at a playground. They get out and walk up to the river, where there’s a concrete walkway running for miles along it. 

Next to Dean, Cas has the jacket pulled tight around him. Dean sees him nuzzle into the collar.

“Dude. Did you just smell my jacket?”

Cas jerks his head up, apparently not realizing  that Dean was watching. “Um…”

“Does it smell bad or something?”

“Oh, n- no. It. It, uh. Smells like… you.”

Dean looks down at his feet, willing his heart to stop beating so quickly. If this keeps up, he’s going to seem out of breath even though they’re walking slowly. 

“Is that good or bad?” He asks cautiously. 

“Good.” Says Cas. “You smell good.”

“Oh.” Dean clears his throat. “Good.”

They walk a little more, and Dean can’t help stealing looks when Cas isn’t looking. His hair is windblown, his cheeks are flushed, he looks small in Dean’s jacket. 

“Do you want your jacket back?” Cas asks, catching Dean looking. 

“Nah.” He says. He takes a breath, “It looks better on you anyway.”

Cas laughs, rolling his eyes. “What _ever_.”

“What? What do you mean “whatever”?”

Cas huffs. “It looks better on you and you know it.”

“Dude.”

“What?”

“Dude.”

“ _What_?”

“You’re kidding me, right? You look fucking cute in it.”

Cas stops walking abruptly, and Dean, realizing what he’s said, tries to backtrack. “Uh. I mean, you look… good? Nice. You- you, uh, it’s a good look.”

Cas just stands there, looking at him. His mouth is open. “Huh.” He says. 

Dean swallows and keeps walking, and a few seconds later Cas catches up to him. They walk past statues and memorials and a few gazebos, then Cas sees a bench, facing the water, and he goes to it. Dean follows. They sit down side-by-side and Dean stretches his arms out across the back of the bench without thinking about it. Cas burrows into his side, head leaning on Dean’s shoulder. His fluffy, flyaway hair is right next to Dean’s face, and he catches himself smelling it. It smells vaguely like something fruity, and for some reason it makes Dean’s heart clench oddly. 

Dean turns his head and looks down at their legs, next to each other. Dean’s in thick denim, Cas’ in thin, stretchy fabric. His knees look sort of knobby, and they appear to be trembling. Dean reaches out and puts his hand on Cas’ leg, maybe a little further up than he ought to. 

“You still cold?” He asks.

“Only a little.” Says Cas.

“Well, um,” Dean looks down at himself, trying to think of something he can give Cas to help him warm up, but he’s drawing a blank. It would be weird to offer the guy his shirt, wouldn’t it? Yeah, that would be weird. And anyway then he’d freeze himself, and what good would that do him?

Beside him, Cas laughs. “Dean Winchester, you’re trying to figure out how to keep me warm, aren’t you?”

“Um, yeah.” 

“I’m a big boy.” Cas tells him. “I can deal with a little cold.”

“Yeah, but I don’t want you to be cold.”

Cas stares at him. “You’d give me the shirt off your back if I asked for it, wouldn’t you?”

“Well, yeah. I mean- if you needed it.”

Cas’ eyes go soft at the corners, he smiles. “You’re something else.”

Dean huffs. “ _You’re_ somethin’ else.” He grumbles. 

Cas laughs again, a sound that Dean thinks he’ll never, ever get tired of. “Dean.” He says.

Dean looks away, but then Cas’ voice comes again, “Dean.” and there’s a hand on his jaw, gently turning his head back toward his friend. 

And then he’s right there, nose to nose with Cas, who’s looking at him like he’s something wonderful. And then Cas is leaning forward, brushing their lips together gently in a kiss that’s barely, barely there, but still sort of makes Dean feel like he’s going to have a heart attack. 

When Cas pulls back, Dean follows, and presses his lips to Cas’. This kiss is gentle too, but more firm. There’s no mistaking what it is, and he feels Cas’ fingers curl against his jaw, long and lithe. He kisses Cas again, and then Cas kisses him again, and then _they’re_ kissing, together. Long, drawn out kisses, punctuated by little breaths, highlighted by Dean’s hand kneading at Cas’ thigh, at Cas’ fingers sliding up into Dean’s hair.

They kiss for several minutes before Cas pulls back, looking dazed. His eyes are bright and his lips are red and spit-slick, he looks like he might fall over if he weren’t sitting down. 

“Well then.” He says, voice so quiet it’s almost a whisper. 

Dean clears his throat. He looks away for a moment, and when he looks back, Cas is smiling at him. He reaches over and squeezes Dean’s knee. 

“You ready to go home?” He asks.

“Yeah,” Dean says, “I think so.”

 

They go back to Dean’s, and Cas keeps smiling. Hell, Dean does too. He’s happy, alright? This? This is good. He’s not exactly sure what it is yet, but if it’s with Cas it’s sure to be good. 

They sneak into the house, back to Dean’s room, and suddenly Dean feels a little… well… not exactly uncomfortable. More like, uncertain. The room seems like something different now. 

Cas, of course, gets right to the heart of things. As he does.

  
“Things… don’t have to be different,” He says, standing in front of Dean. “Just because we kissed. If you feel uncomfortable, it doesn’t have to mean anything.”

Dean shakes his head. “I’m not- not uncomfortable. Just… I don’t know what I’m doin’, man.”

Cas nods like he understands. He probably does. 

“What do you want?” He asks.

Dean is quiet while he thinks, and he can see the worry in Cas’ eyes. But it’s buried deep, under layers of patience and kindness and understanding. Fuck, what did he ever do to deserve Cas?

“You.” He says finally. “I want you.”

Cas lets out a relieved sigh, and the smile he gives Dean is the loveliest smile in the world. He steps forward and loops his arms around Dean’s neck. 

“Perfect.” He whispers, pressing his lips to Dean’s. “You’re perfect.”

Dean shakes his head, but he’s too busy kissing Cas to speak, and then eventually he forgets about it, lost in the feel of Cas’ tongue in his mouth, Cas’ hands in his hair.

They kiss for a while, and then, inexplicably, something changes. Dean can’t pinpoint it, say what it is, he just knows that one moment the kissing is lazy and unhurried and the next moment they’re definitely moving toward _something_. Cas is pressing closer, his breaths are coming faster, Dean feels arousal curl in his gut. 

He reaches up and pushes his jacket off of Cas’ shoulders, letting it fall to the floor with a thump, and how he can touch more. Now he can press his hands up under Cas’ shirt to feel his skin. 

Cas is pulling him, back toward the bed. He climbs up on it and leans back on the pillows and waits, looking beautiful and… a little debauched. 

Dean climbs up over him until his knees bracket Cas’ hips. He pulls his shirt over his head and tosses it to the ground before leaning down to kiss Cas again. Cas moans into the kiss, hands coming up to grip Dean’s shoulders. Dean loses track… of everything. Time means nothing, not with Cas under him, making all these noises. 

Cas sits up, struggling to pull his sweater over his head, and Dean is more than happy to help him get it off. Off goes Cas’ shoes, and Dean’s, then the tights. 

Taking off Cas’ tights is an experience, peeling them down over his friend’s thick thighs is a thing of beauty, and it makes him feel unstable and desperate. He kneels between Cas’ knees and pushes his skirt up to his hips, revealing a pair of purple cotton panties, so that he can suck bruises onto his pale thighs.  
Cas bucks underneath him, biting his fist to keep from making too much noise. His erection is straining against his underwear, there’s a wet spot where the tip is, and Dean takes some time to suck on it through the fabric before he pulls it down, beneath Cas’ balls. 

He’s never given a blowjob before, but god he tries. He gives it everything he’s got, he treats Cas’ cock like it’s something to be worshiped, and hopes that’s enough. It seems to be, because Cas comes quickly, arching his back and groaning into his elbow, all over his stomach. After, Cas takes Dean in hand, and he comes as well.

They get tissues from Dean’s night table and clean up before getting new pajamas and curling up together in Dean’s bed. Dean almost feels like this should be awkward, but it’s Cas. Cas is his best friend. He’s known Cas forever, everything is easy with Cas. Even this, it seems.

He sighs. 

“Best Halloween ever.” He says.

Cas laughs, and everything is good.

**Author's Note:**

> You can find me [here](https://deanlightful.tumblr.com/), on tumblr.


End file.
